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There are many instances in which Bobby refers to Sherman as a "blonde pretty-boy", indicating that he bears semblance to a bishonen. He is denoted to be tall, notably taller than Bobby, and has more "handsome" and "refined" features. One of his most prominent aspects is his blonde hair, which falls slightly below his shoulders in a rather messy manner.

However, there are a few occasions in the story when Sherman ties up his hair into a ponytail, which helps reinforce his "refined gentleman" appearance. With his hair tied up, Sherman appears much more serene and thoughtful when compared to his other look.

“Ayame, don’t get the wrong impression of Sherman. He seems mature at first, but he’s actually a complete goof.”

- Bobby Topalis, Act II: Chapter 4 of A Different Perspective

At first glance, Sherman appears to be quiet and reserved. When first meeting him, Ayame noted that he gave off a "mature" aura of sort, murmuring that he looked respectable. He uses advanced vocabulary and an elegant way of speaking when interacting with strangers or people he has just met. Thanks to this, Sherman is somewhat well known around the school as being a bit of a ladyslayer or a casanova, and gets a lot of attention from random girls walking around him.

However, this is actually just a facade; Sherman hides a light-hearted, jovial, and overall goofy personality underneath. He's a bit of a gadfly and likes to instigate trouble for the sake of it, and is also a bit of an open pervert around people he is comfortable around, such as Bobby or Niles O'Neill. These two aspects were most prominently shown when he assembled a personal "Pervert Squad", to which he taught lessons about perception and detail. He himself is quite good at piecing together clues, such as when he noticed that Kyoichi Akikawa was a pervert through how his eyes subtly "scanned" both his and Megumi's entire body when they first met in Silver Blizzard.

Even with his odd quirks, however, at the core Sherman is utterly devoted to the people he cares about; notably, his twin sister Megumi and his childhood friend Bobby. He is always able to read their minds from the slightest clues; in A Different Perspective, he figured out that Megumi wished for a sort of parental figure to replace their parents, and as such attempted to take on the role, putting enormous pressure on himself in the process.

In Silver Blizzard, it is revealed that Sherman is also somewhat lazy and messy. This was heavily glossed over in A Different Perspective mainly because of Bobby's feelings of regret and remorse when he was writing that story. This was mainly thanks to his comatose state at the time.

In addition, Silver Blizzard reveals that Sherman is actually a somewhat insecure person who does not fully see himself as worthy of the attention he gets, especially from his close friends. He is weighed down by guilt from his memories of Inori, as he thinks that he has taken his life down the wrong road, rather than making the most of his second chance. This is made worse by Sherman's flashback-esque dreams of Inori as the tenth anniversary of the plane crash passes by. Sherman is also aware of Bobby's admiration and close bond with him, and does not see himself as worthy of this attention. When writing A Different Perspective, Bobby had no idea of this; as such, it was omitted in the story.

In both stories Sherman and his sister are born in America, but annually visit their relatives in Japan. During one such visit, when they were seven years old, a plane crashed into the hotel they were staying at. Sherman's parents were killed in the crash; though Megumi was unharmed, he himself received a concussion from rubble and twisted his ankle trying to protect her.

Though Sherman was unable to walk due to his hurt ankle, a heavily injured girl approached him and escorted him and Megumi outside of the vicinities safely. This moment, along with the girl's own physical state and mood, was a memory that would haunt him for a long time.

He had no way of knowing this, but this girl was Inori Akikawa, Kyoichi's older sister.

Over time, Sherman's consciousness began to develop a defense system to protect his mind from the traumas of the incident; notably, by covering them up with humor and open perversion. Though this prevented him from having traumatic flashbacks like Megumi, it also sculpted Sherman's growth as he grew older; he became a lighthearted, perverted person as a result.

In addition, thanks to injuries he obtained in the crash, a moderate amount of toxins entered Sherman's bloodstream. Against all odds, the majority of his cardiovascular system defied science and was miraculously able to adapt to the toxin, effectively immunizing him from the normal autotoxemia that he would have obtained otherwise. However, there was a major side effect to this: certain sections of Sherman's heart never adapted to the toxin, and as he grew older his heart began to weaken.

Sherman was not mentioned at all by Miu, so it is uncertain what his fate was in Miu's timeline. However, in the timeline created directly after Miu altered the time stream, Sherman is unable to cope with his traumas and the haunting memories of Inori and is eventually driven insane and taken to an asylum. Because he is not present to provide support, the original timeline's Bobby is unable to tackle many of his challenges in Act II, such as talking down Tsukiya Shiranui on the class trip.

Due to their parents' deaths, Megumi and Sherman have always been very close, though not at the level of lovers like Yukiha and Haya. Sherman cares for his twin sister more than anyone else, and is always willing to do anything for her. Interestingly enough (ADP only), he acts like Megumi's pseudo-parent at times, taking the place of their real parents to go out on errands, spend time with her, or even reprimand her.

In Silver Blizzard, it's the opposite; Megumi often acts as Sherman's pseudo-parent. She often looks out for him like a parent would.

Even in their childhood friend group, Sherman and Bobby have always been extremely close, enough so that they could practically be brothers. Sherman cares for Bobby at an equal level to Megumi and is always willing to help no matter what the situation is. In fact, he knows Bobby so well that he is usually able to quickly identify Bobby's emotions, no matter how hard he tries to hide it.

After the end of Silver Blizzard's Act II, however, the comatose Sherman is revived after receiving a heart transplant from Bobby. Though he doesn't reveal it to the others at first, Sherman soon realizes that the cellular memory phenomenon had effectively transferred several of Bobby's memories and thoughts into his own. As such, at the end of this timeline, Sherman fully and completely understands Bobby's actions and his reasoning behind it.

Akihisa and Sherman have a pretty solid relationship. After Akihisa joined Sherman's "Pervert Squad", he took him under his wing and began to teach and influence him. Akihisa began to look up to Sherman as a mentor figure, and is blindly loyal to him... to a fault.

Sherman was named after Fairy Fencer F's Sherman Shallancer, despite the two having fairly different personalities.

Sherman is the only member of the cast who sleeps on the floor for the majority of the storyline.

Sherman's birthday month and day is the same date that Darkfire545 accepted waifudom.

Compared to the other members of Bobby's friend group, Sherman is the worst driver.

In ADP, Sherman's fate in the hot springs (notably, him being dragged into the girls' side when the signs were switched around) is a blatant reference to Date A Live.

Sherman is the second character in the story to have a chapter named after him (Act II: Chapter 4.5; the first being Yukitsuki in Act I: Chapter 6). However, he is the first and only character whose named chapter is solely a song parody.

In Silver Blizzard, Sherman is the second character to experience the cellular memory phenomenon (the first being Ayame).